Nouveaux réactifs de cyclopentannélation : application à la synthèse de précurseurs de l'ottélione
(2006)
Files
4-thesepartexperimentale.pdf
Open Access - Adobe PDF
- 624.04 KB
2-thesepartietheorique1.pdf
Open Access - Adobe PDF
- 541.94 KB
1-thesetitre.pdf
Open Access - Adobe PDF
- 45.96 KB
5-thesereference.pdf
Open Access - Adobe PDF
- 32.84 KB
3-thesepartietheorique2.pdf
Open Access - Adobe PDF
- 335.68 KB
Details
- Authors
- Supervisors
- Abstract
- (en) This dissertation is consecrated to the development of new reagents for [3+2] cycloaddition allowing the synthesis of five-membered carbocycles. In the first part of this work, we focussed our attention on the synthesis of these reagents, equivalents of 1,3-dipoles, bearing a sulfone as well as an ortho-ester function. We have evaluated the reactivity of this dipoles in [3+2] cycloaddition with enones to form bicyclic compounds.The continuation of this work was consecrated to the study of a sulfonylated homoenolate equivalent bearing a chirality inductor. An original synthetic scheme was developed for the obtention of this reagent enantiomerically pure. Its addition to enones allowed us, after cyclisation, to obtain two separable diastereoisomers. After elimination of the chirality inductor, highly enantiomerically pure hydrindenones were obtained. In the second part of this work, we focussed on the application of the [3+2] annelation reaction to the total synthesis of natural compounds. After the choice of the most suitable orthoester and enone, we have synthesised some intermediates that could be used in otteliones synthesis.
- Affiliations
Citations
Kallah, B. (2006). Nouveaux réactifs de cyclopentannélation : application à la synthèse de précurseurs de l’ottélione. https://hdl.handle.net/2078.5/40281